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EP0389632A1 - Materiau medical glissant et son procede de production - Google Patents

Materiau medical glissant et son procede de production Download PDF

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Publication number
EP0389632A1
EP0389632A1 EP89909234A EP89909234A EP0389632A1 EP 0389632 A1 EP0389632 A1 EP 0389632A1 EP 89909234 A EP89909234 A EP 89909234A EP 89909234 A EP89909234 A EP 89909234A EP 0389632 A1 EP0389632 A1 EP 0389632A1
Authority
EP
European Patent Office
Prior art keywords
group
component
groups
medical material
slippery medical
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
EP89909234A
Other languages
German (de)
English (en)
Other versions
EP0389632A4 (en
Inventor
Ryojiro Akashi
Shoji Nagaoka
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Toray Industries Inc
Original Assignee
Toray Industries Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Toray Industries Inc filed Critical Toray Industries Inc
Publication of EP0389632A1 publication Critical patent/EP0389632A1/fr
Publication of EP0389632A4 publication Critical patent/EP0389632A4/en
Ceased legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L29/00—Materials for catheters, medical tubing, cannulae, or endoscopes or for coating catheters
    • A61L29/08—Materials for coatings
    • A61L29/085—Macromolecular materials
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
    • A61L27/28—Materials for coating prostheses
    • A61L27/34—Macromolecular materials
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L31/00—Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
    • A61L31/08—Materials for coatings
    • A61L31/10—Macromolecular materials
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
    • Y10T428/31573—Next to addition polymer of ethylenically unsaturated monomer
    • Y10T428/31576—Ester monomer type [polyvinylacetate, etc.]
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31678—Of metal
    • Y10T428/31692—Next to addition polymer from unsaturated monomers
    • Y10T428/31699—Ester, halide or nitrile of addition polymer
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31786—Of polyester [e.g., alkyd, etc.]
    • Y10T428/31797—Next to addition polymer from unsaturated monomers
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31855—Of addition polymer from unsaturated monomers
    • Y10T428/31909—Next to second addition polymer from unsaturated monomers
    • Y10T428/31928—Ester, halide or nitrile of addition polymer

Definitions

  • the present invention relates to a medical material wherein a hydrophilic coating exhibiting excellent low frictional property, namely, easily-slippery property on wetting is formed on the surface of a base material and a method for preparation thereof.
  • low frictional property easily-slippery property of the surface is one of the essential requirements.
  • these materials have no easily-slippery property, when a catheter is inserted in a human body, there is the possibility that a pain could be accompanied with it or a damage or an inflammation of tissue mucosa could occur.
  • the method wherein the surface of a base material is coated with a variety of oils exhibits low durability and has a problem of safety due to eluates.
  • the method wherein it is coated with a polymer having a low friction coefficient such as Teflon hardly exhibits sufficiently an easily-slippery property.
  • the method of coating with a hydrophilic polymer exhibits an easily-slippery property being superior to these methods but there is a problem on its durability.
  • the purpose of the present invention is to offer a technology providing an excellent easily-slippery property which solves the problems of these conventional technologies.
  • the present invention is an easily-slippery medical material wherein the surface of a base material coated with the following component A is coated with the following component B
  • the present invention provides a medical material having..excellent easily-slippery property and durability which.conventional technologies have never been able to provide obtained by fixing a hydrophilic polymer on the surface of a base material through a covalent bonding and a method for preparation thereof.
  • the reactive functional group of the component A in the present invention is such a group that can react with the reactive heterocyclic group of the component B and those which are rich in anionic or cationic characteristics so as to open the heterocyclic ring.are cited.
  • alkali metal such as lithium, sodium and potassium alcoholate groups, primary and secondary amino groups, alkali metal amide groups, carboxylic acid group, sulfonic acid group, Grignard reagents such as magnesium halide group, fluorinated boron complex groups etc.
  • amino groups are preferably used as they are highly reactive.
  • the polymer having such a reactive functional group which is the component A, partially hydrolyzed products with alkali of polyvinyl acetate, hydrolyzed products with alkali of polymers having vinyl acetate as a copolymerizable component, alkali-treated products (alcoholates) of polymers having 2-hydroxyethyl (meth)-acrylate as a copolymerizable component, hydrolyzed products (aminated products) of polyisocyanates, polymers having aminomethylstyrene as a copolymerizable component and amidated products thereof with alkali metals, polymers having styrene derivatives containing various amino groups such as 2-aminoethyl-4-vinyl-phynetylamine as a copolymerizable component and amidated products thereof with alkali metals, polymers having (meth)acrylic acid as a copolymerizable component, polymers having sulfonated styrene as a copol
  • alkali-hydrolyzates of ethylenevinyl acetate copolymers, vinyl chloride-vinyl acetate copolymers and methyl (meth)acrylate-vinyl acetate copolymers and acrylonitrile-vinyl acetate copolymers alkali-treated products of methyl (meth)acrylate-2-hydroxyethyl (meth)acrylate copolymers, styrene-2-hydroxyethyl (meth)acrylate copolymers, acrylonitrile-2-hydroxyethyl (meth)acrylate copolymers, styrene- hydroxystyrene copolymers and methyl (meth)acrylate- hydroxystyrene copolymers, hydrolyzates (aminated products) of adducts of diphenylmethane-4,4'-diisocyanate or hexamethylenediisocyanate with trimethylo
  • the content of said reactive functional groups in said component A is variably selected in accordance with the bonding force with the component B and the adhesive force and preferably selected in the range of 0.1 - 50 wt.%.
  • the range of 1 - 30% is especially preferable.
  • the reactive heterocyclic group in the component B in the present invention any heterocyclic group which can react with the reactive functional group of the component A can be used, but those ring structures which have high strain are preferable from the viewpoint of high reactivity.
  • Ethylene oxide group is especially preferably selected as it is easily used.
  • the content of said reactive heterocyclic group in said component B is variably selected in accordance with the aimed characteristics, 0.01 - 50 wt.%, especially 0.1 - 30 wt.% is preferable in terms of the amount of the side chains containing the reactive heterocyclic group.
  • the hydrophilic polymers having said reactive heterocyclic groups which are the component B, can be prepared by either of the following methods, namely, a method (1) wherein a monomer having a reactive heterocyclic group is copolymerized with a hydrophilic monomer and a method (2) wherein a compound having a reactive heterocyclic group is reacted with and thereby introduced in a hydrophilic polymer.
  • (meth)-acrylamide-glycidyl (meth)acrylate copolymers N-vinyl-2-pyrrolidone-glycidyl (meth)acrylate copolymers, monomethoxytriethylene glycol mono(meth)acrylate-glycidyl (meth)acrylate copolymers, monomethoxytetraethylene glycol mono(meth)acrylate-glycidyl (meth)acrylate copolymers, polyethylene glycol mono(meth)acrylate-glycidyl (meth)-acrylate copolymers, 2-hydroxyethyl (meth)acrylate-glycidyl (meth)acrylate copolymers, (meth)acrylamide-glycidyl vinyl benzoate copolymers, N-vinylpyrrolidone-glycidyl vinyl benzoate copolymers, polyethylene glycol mono(meth)acrylate-glycidyl vinyl benzoate copolymers,
  • the content of the reactive heterocyclic vinyl monomer is properly selected in accordance with the aimed characteristics and it is preferably in the range of 0.01 - 50 wt.% not to spoil the hydrophilic nature. Moreover, to impart physical strength to the hydrophilic polymer, it is preferably to copolymerize a hydrophobic monomer as the third component. In this case, the content of the third component is not specifically restricted as far as the hydrophilic nature is not spoiled, but the range of 0.01 - 50 wt.% is preferable.
  • hydrophobic monomers alkyl (meth)-acrylates, vinyl chloride, vinylidene chloride, ethylene, (meth)acrylonitrile, propylene, vinyl acetate, styrene and styrene derivatives are cited.
  • molecular weight of these polymers polymers having a molecular weight of 1,000 - 5,000,000 can be used and 100,000 - 2,000,000 is preferable.
  • hydrophilic polymer such as cellulose, cellulose derivatives (methyl cellulose, ethyl cellulose, carboxymethylcellulose, cyanoethylcellulose, cellulose acetate,sodium salt of cellulose nitrate), amylose, amylopectin, alginic acid, heparin, pectin and watersoluble nylon are reacted with a compound of the following formula (VI) and a reactive heterocyclic ring is thereby introduced, are cited.
  • the content of introduction of the reactive heterocyclic ring is not especially restricted as far as the aimed hydrophilic nature is not spoiled, but the range of 0.01 - 50 wt.% is preferable.
  • the hydrophilic coatings of the present invention have good easily-slippery property and durability caused by said constitution, but it is a desirable method to cure the component B after coating for improving the durability furthermore. Namely, it is possible to improve the physical strength without lowering the easily-slippery property by providing a three dimensional network structure.
  • the method for curing (crosslinking) like this, it is possible to apply generally various physicochemical means. For example, a method wherein said polymer is cured (crosslinked) by generating active radicals by using light, heat or radiation and moreover, a polymerizable polyfunctional monomer is therein additionally added. As a method for generating efficiently active radicals, it is preferable to use peroxides and azo compounds.
  • peroxides having a strong capability of drawing hydrogen.
  • acetyl peroxide, cumyl peroxide, propionyl peroxide, benzoyl peroxide, tert-butyl performate, potassium persulfate etc. are cited.
  • the loading of these compounds to the component B is properly selected in accordance with the aimed characteristics, but the range of 0.001 - 20 wt.% is preferable.
  • polymerizable polyfunctional monomer which can be incorporated to cure (crosslink) furthermore efficiently, divinylbenzene, ethylene glycol di(meth)acrylate, trimethylolpropane or pentaerythritol di-, tri- or tetra- (meth)acrylate, diethylene glycol or polyethylene glycol di(meth)acrylate can be cited.
  • the loading of these compounds to the component B is properly selected in accordance with the aimed characteristics, but the range of 0.1 - 30 wt.% is preferably selected.
  • the base material is variably selected in accordance with the purpose of use and various plastics, inorganic materials and metallic materials are suitably used.
  • plastics, inorganic materials and metallic materials are suitably used.
  • polyvinyl chloride, polyethylene, polypropylene, polystyrene, polyurethane, polyurea, polymethyl methacrylate, nylon, polyester, polyacrylonitrile, metallic wires coated therewith, stainless steel, elastic metals, ceramics and wood are cited.
  • dipping or spin coating is carried out by using a solution wherein a specified amount of the component A is dissolved in a proper good solvent and then drying is done.
  • solvents to be used alcohols, aromatic hydrocarbons, linear or cyclic hydrocarbons, halogenated hydrocarbons, ketones and amides are preferable.
  • concentration of the component A in the solution can be properly selected in accordance with the aimed thickness of coating, but the range of 0.01 - 50 wt.% is preferably used. The range of 1 - 10 wt.% is especially preferable.
  • the surface of a base material coated with the component A is coated with the component B.
  • the method of coating is the same as the method of coating for the component A, namely, dipping or spin coating is carried out by using a solution wherein a specified amount of the component B is dissolved in a proper good solvent and then drying is done.
  • a solution wherein a specified amount of the component B is dissolved in a proper good solvent and then drying is done.
  • water can be also used.
  • the concentration of the component B in the solution can be properly selected in accordance with the aimed thickness of coating, but the range of 0.01 - 50 wt.% is preferably used. The range of 1 - 10 wt.% is especially preferable.
  • a curing (crosslinking) agent such as peroxides, azo compounds and polymerizable polyfunctional monomers is used, it is preferable that the specified amount thereof is added in this solution.
  • a reaction of the component A with the component B is carried out by carrying out successively by a heat treatment.
  • the heating condition, the time and the temperature are properly selected in accordance with the nature of the reaction and existence of a curing (crosslinking) reaction and one of the preferable range is 30 - 200°C and 1 min - 24 hr. It is also a preferable method to carry out the reaction in various inert gases for suppressing side reactions.
  • acrylamide-glycidyl methacrylate copolymer having a molecular weight of about 200,000 was obtained by polymerizing 9.0 g of acrylamide and 1.0 g of glycidyl methacrylate in dimethyl sulfoxide (DMSO) by using AIBN (azobisisobutyronitrile) as an initiator.
  • DMSO dimethyl sulfoxide
  • a wire having a diameter of 2 mm prepared by coating a stainless wire with a polyurethane was immersed in a 2% polyisocyanate (manufactured by Nippon Polyurethane Industries Co., Ltd., The name of the product: C-L, TDI/TMP adduct) solution in methyl ethyl ketone (MEK) for 1 min and the coated wire was dried at 50°C for 1 hr. Then, this was immersed in 0.1N sodium hydroxide ag. solution at 40°C for 1 hr to hydrolyze it and to form amino groups.
  • a 2% polyisocyanate manufactured by Nippon Polyurethane Industries Co., Ltd., The name of the product: C-L, TDI/TMP adduct
  • MEK methyl ethyl ketone
  • this wire was immersed in a 5% acrylamide-glycidyl methacrylate copolymer aq. solution for 5 sec and pulled up and the reaction was carried out at 100°C for 5 hr.
  • the obtained wire coated with the hydrophilic coating exhibited excellent easily-slippery property when it was wetted with a physiological saline or water and also exhibited excellent easily-slippery property after 1 hr boiling, which meant excellent durability.
  • methyl methacrylate-2-hydroxyethyl methacrylate copolymer having a molecular weight of about 100,000 was obtained by polymerizing 8.0 g of methyl methacrylate and 2.0 g of 2-hydroxyethyl methacrylate in isopropyl alcohol by using AIBN (azobisisobutyronitrile) as an initiator.
  • AIBN azobisisobutyronitrile
  • Example 2 the same wire as that of Example 1 was immersed in a 3% solution of this polymer in dioxane for 1 min and dried at 50°C for 1 hr. Furthermore, this was immersed in 1N sodium hydroxide aqueous solution to form sodium alcoholate.
  • Example 2 the same compound as that of Example 1 was used and was reacted by means of the same method.
  • the obtained wire coated with the hydrophilic coating exhibited excellent easily-slippery property when it was wetted with a physiological saline or water and also exhibited excellent easily-slippery property after 1 hr boiling, which meant excellent durability.
  • N-vinylpyrrolidone-glycidyl acrylate copolymer having a molecular weight of about 300,000 was obtained by polymerizing 9.0 g of N-vinylpyrrolidone and 1.0 g of glycidyl acrylate by using V-65 (azobisvaleronitrile) as an initiator.
  • Example 1 The same treatment as that of Example 1 was performed by using the same materials as those of Example 1 as both a component A and a base material (wire).
  • this wire was immersed in 3% solution of the previously synthesized N-vinylpyrrolidone-glycidyl acrylate copolymer in chloroform for 5 sec, pulled out therefrom, dried and reacted at 100°C for 5 hr.
  • the obtained wire coated with the hydrophilic coating exhibited excellent easily-slippery property when it was wetted with a physiological saline or water and also exhibited excellent easily-slippery property after 1 hr boiling, which meant excellent durability.
  • a hydrophilic coating was formed by the same method as that of Example 3 except using N-vinylpyrrolidone-vinyl acetate-glycidyl acrylate copolymer having a molecular weight of about 500,000 obtained by polymerizing 7.0 g of N-vinylpyrrolidone, 2.0 g vinyl acetate and 1.0 g of glycidyl acrylate in ethyl alcohol by using V-65 (azobisvaleronitrile) as an initiator as a component B.
  • V-65 azobisvaleronitrile
  • the obtained wire exhibited excellent easily-slippery property when it was wetted with a physiological saline or water and it was found that it exhibited excellent easily-slippery property after 1 hr boiling and had excellent durability.
  • a hydrophilic coating was formed by the same method as that of Example 3 except using N-vinylpyrrolidone-ethyl acrylate-glycidyl acrylate copolymer having a molecular weight of about 600,000 obtained by polymerizing 8.0 g of N-vinylpyrrolidone, 1.5 g of ethyl acrylate and 0.5 g of glycidyl acrylate in isopropyl alcohol by using V-65 as an initiator as a component B.
  • V-65 an initiator
  • the obtained wire exhibited excellent easily-slippery property when it was wetted with a physiological saline or water and it was found that it exhibited excellent easily-slippery property after 1 hr boiling and had excellent durability.
  • monomethoxytetraethylene glycol monomethacrylate-glycidyl vinyl benzoate copolymer having a molecular weight of about 1000,000 was obtained by polymerizing 9.5 g of monomethoxytetraethylene glycol monomethacrylate and 0.5 g of glycidyl vinyl benzoate in tetrahydrofuran by using AIBN (azobisisobutyronitrile) as an initiator.
  • AIBN azobisisobutyronitrile
  • Example 2 The same component A and base material (wire) as those of Example 2 were used and treated with the same method as that of Example 2. Then, this wire was immersed in 5% previously synthesized monomethoxytetraethylene glycol monomethacrylate-glycidyl vinyl benzoate copolymer solution in dimethylacetamide for 5 sec, pulled up, dried and reacted at 100°C for 5 hr.
  • the obtained wire exhibited excellent easily-slippery property when it was wetted with a physiological saline or water and it was found that it exhibited especially excellent easily-slippery property after 1 hr boiling and had excellent durability.
  • a hydrophilic coating was formed by the same method as that of Example 3 except adding 1% of benzoyl peroxide (based on the polymer) to N-vinylpyrrolidone-glycidyl acrylate copolymer and carrying out the reaction under reaction conditions which were at 120°C, for 5 hr under nitrogen atmosphere.
  • the obtained wire exhibited excellent easily-slippery property when it was wetted with a physiological saline or water and it was found that it exhibited especially excellent easily-slippery property after 1 hr boiling and had excellent durability.
  • a hydrophilic coating was formed by the same method as that of Example 4 except adding 1% of benzoyl peroxide (based on the polymer) and 5% of tetraethylene glycol dimethacrylate (based on the polymer) to N-vinylpyrrolidone-vinyl acetate-glycidyl acrylate copolymer used in Example 4 and carrying out the reaction under reaction conditions which were at 120°C for 5 hr under nitrogen atmosphere.
  • the obtained wire exhibited excellent easily-slippery property when it was wetted with a physiological saline or water and it was found that it exhibited especially excellent easily-slippery property after 1 hr boiling and had excellent durability.
  • Example 2 The same polyurethane-coated wire as that of Example 1 was immersed in 2% polyisocyanate (manufactured by Nippon Polyurethane Industries Co., Ltd., The name of the product: C-L, TDI/TMP adduct) solution in methyl ethyl ketone (MEK) for 1 min and dried at 50°C for 1 hr. Then, this was immersed in 4% polyvinylpyrrolidone (manufactured by Polysciences, Inc., the molecular weight was 360,000) solution in chloroform for 5 sec, pulled up, dried and then reached at 80°C for 5 hr.
  • polyisocyanate manufactured by Nippon Polyurethane Industries Co., Ltd., The name of the product: C-L, TDI/TMP adduct
  • MEK methyl ethyl ketone
  • the obtained wire When the obtained wire was wetted with a physiological saline or water, it exhibited excellent easily-slippery property at the beginning, but after a repeated test of several times or boiling for several min, it exhibited no easily-slippery property at all and as the result, it was found that the durability was poor.
  • a sample was prepared by the same method as that of Comparative Example 1 except using polyethylene glycol (the molecular weight was 6,000) as a hydrophilic polymer.
  • the obtained wire did not exhibit good easily-slippery property when it was wetted with a physiological saline or water and it became not to exhibit easily-slippery property at all after a repeated test of several times or boiling for several min and as the result, it was found the durability was poor.
  • the easily-slippery material of the present invention can be widely applicable in a variety of fields. Above all, as this material has both excellent easily-slippery property and durability (safety), it is applicable for medical materials such as catheters, guide wires, endoscopes, contact lenses and condom. Moreover, it has excellent biocompatibility as it has a hydrophilic nature and when it is applied for medical materials, it is expected that besides said characteristics, such excellent characteristics as high anti-thrombus characteristics can be obtained.

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  • Health & Medical Sciences (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Chemical & Material Sciences (AREA)
  • Dermatology (AREA)
  • Medicinal Chemistry (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Transplantation (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Surgery (AREA)
  • Vascular Medicine (AREA)
  • Materials For Medical Uses (AREA)

Abstract

Un matériau médical qui présente d'excellentes propriétés de glissement et de durabilité sans égal dans l'état antérieur de l'art comprend un matériau de base à la surface duquel est fixé un polymère hydrophile par de fortes liaisons covalentes. Son procédé de production est également décrit.
EP19890909234 1988-08-09 1989-08-09 Slippery medical material and process for its production Ceased EP0389632A4 (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP19929488 1988-08-09
JP199294/88 1988-08-09
JP96952/89 1989-04-17
JP9695289 1989-04-17

Publications (2)

Publication Number Publication Date
EP0389632A1 true EP0389632A1 (fr) 1990-10-03
EP0389632A4 EP0389632A4 (en) 1990-12-27

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
EP19890909234 Ceased EP0389632A4 (en) 1988-08-09 1989-08-09 Slippery medical material and process for its production

Country Status (5)

Country Link
US (1) US5079093A (fr)
EP (1) EP0389632A4 (fr)
KR (1) KR900701332A (fr)
DK (1) DK85590A (fr)
WO (1) WO1990001344A1 (fr)

Cited By (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1991019756A1 (fr) * 1990-06-15 1991-12-26 Meadox Surgimed A/S Procede destine a former un revetement hydrophile et a coefficient de friction faible sur un instrument medical, et instrument medical pourvu d'un tel revetement
EP0611576A1 (fr) * 1993-02-08 1994-08-24 Terumo Kabushiki Kaisha Outil médical avec une surface lubrifiante dans un milieu humide et méthode pour sa fabrication
EP0693948A4 (fr) * 1993-05-12 1995-12-07 Target Therapeutics Inc Catheters lubrifies
EP0693293A1 (fr) * 1994-07-07 1996-01-24 Terumo Kabushiki Kaisha Instruments médicaux présentant des propriétés lubrifiantes superficielles à l'état mouillé
WO1996003164A1 (fr) * 1994-07-22 1996-02-08 Advanced Cardiovascular Systems, Inc. Materiau de revetement hydrophile a usage intracorporel
EP0728487A1 (fr) * 1995-02-22 1996-08-28 Meadox Medicals, Inc. Méthode pour obtenir un revêtement hydrophile sur un substrat et substrats, en particulier instruments médicaux, avec ces revêtements
NL1001746C2 (nl) * 1995-11-27 1997-05-30 Belden Wire & Cable Bv Geleidedraad voor medische toepassing.
WO1998058989A1 (fr) 1997-06-20 1998-12-30 Coloplast A/S Revetement hydrophile et procede de preparation dudit revetement
WO1999038545A1 (fr) * 1998-01-30 1999-08-05 Advanced Cardiovascular Systems, Inc. Revêtement hydrophile lubrifiant pour dispositif médical intracorporel
WO1999040954A1 (fr) * 1997-06-18 1999-08-19 Boston Scientific Corporation Procede de revetement de substrat au moyen d'un enduit biocompatible
US6033720A (en) * 1995-06-30 2000-03-07 Meadox Medicals, Inc. Guidewire having a coated tip
US6179817B1 (en) 1995-02-22 2001-01-30 Boston Scientific Corporation Hybrid coating for medical devices
US6468649B1 (en) 1995-02-22 2002-10-22 Scimed Life Systems, Inc. Antimicrobial adhesion surface
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US8703048B2 (en) 2008-06-16 2014-04-22 Coloplast A/S Buffered swelling media for radiation sterilized hydrophilic coatings
WO2011061295A1 (fr) 2009-11-19 2011-05-26 Blue Medical Devices Bv Cathéter à ballonnet médical extensible à libération de composition et profil étroit
WO2011076217A1 (fr) 2009-12-21 2011-06-30 Coloplast A/S Supports de mouillage à base d'un polyol à bas poids moléculaire et tampon
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WO1990001344A1 (fr) 1990-02-22
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DK85590A (da) 1990-06-11
US5079093A (en) 1992-01-07

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